


Looking for a Second Poker Player

by damnitlaura



Category: Supernatural
Genre: Incest, M/M, Prostitute Sam Winchester, not really tho, they're just roleplaying
Language: English
Status: Completed
Published: 2018-08-05
Updated: 2018-08-05
Packaged: 2019-06-22 03:57:07
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,789
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15573228
Author URL: https://archiveofourown.org/users/damnitlaura/pseuds/damnitlaura
Summary: Dean cruises down the street looking for some fun.





	Looking for a Second Poker Player

**Author's Note:**

  * For [merakieros](https://archiveofourown.org/users/merakieros/gifts).



> This has been sitting in my fics folder for years and I've finally gotten around to posting it. 
> 
> Unbeta'd. All mistakes are my own.

Its dark, past midnight and the street is, to the untrained eye, deserted, but not for Dean. He can make out the shapes of the street walkers against the shadowed walls of the closed shops; he can make out their skimpy clothes and the come-hither gestures they make at him, they all know why he’s slowly rolling down the street, as the impala eases by. 

A short brunette catches his eye, she’s standing under a pool of yellow light, her hair is long, cascading down her back and framing her face in soft curls. Her eyes are large, framed in back and despite the obscenely short skirt, and see through white shirt manage to look innocent. She winks at him as the impala comes to a complete stop. She steps out of the halo of light, the boots of her heels clicking against the concrete floor, she stopped inches away from the door and braced herself against it, the neck of her shirt going askew and revealing the generous set of breast that were partly visible through her shirt. She licks her cherry red lips and in a sultry voice asks

“Hey there big boy, you look like you could use some company.”

Dean smiles and in a husky voice answers, 

“I am feeling a little lonely; know where I can find a number 2 poker player?”

The woman takes a glance at his crotch and visibly deflates, her lips purse and before walking away says,

“If you change your mind, I’ll be around these parts till 3am.”

She pushes herself off the car door and he hears her mutter something to the darkness then take her place again under the street lamp. 

A mammoth of a man with shoulder length brown hair walks out from the shadows; he’s wearing a wife beater that looks like it had been painted on, his ripped jeans are slung low on his hips, revealing a sliver of skin. He walks up to the car with sure steps and doesn’t hesitate to brace a single hand against the door.

“Listen handsome, for 50 I can rock your world with my hand, for 75 I can rock your world with my mouth, and for 100 I’ll make sure you never forget my name.”

The guy must’ve been a new addition to the late night lineup of the street, he was sure he would’ve remembered this guy if he had seen him before. Dean took a moment to study the man, his face was all angles, connected to a thick neck followed by strong, broad shoulders and muscled arms; a narrow waist and legs that just seemed to keep going. Dean audibly swallowed and the tall green eyed stranger tracked the movement of his Adams apple. 

Dean gave a quick nod and motioned for the man to get into his car, after he climbed into the passenger’s seat, Dean continued his drive down the street. 

“What’s it going to be handsome?” Asked the man sitting beside him. 

Dean was curious about how the man’s hand would feel on his dick, wondered if the grip would be smooth or calloused. Then he thought about the man’s mouth, he wondered how those pretty pink lips would feel around his cock, sucking him hard and deep. He also imagined holding that narrow waist, gripping it tight until his fingers left bruises as he slammed into him.

But that wasn’t what he was looking for tonight, tonight Dean wanted to be bent over and fucked raw. He wanted to be pinned down and pounded into the mattress until he was a withering mess of flesh, to the point that he felt like he had no bones and would feel it for days to come. 

“I hope your name isn’t easy to remember.” Dean said as he pulled into the parking lot of the motel at the end of the street. He eased the impala into an empty parking space and headed to the wall that had an opened window with an attached sign that marked it as “Office”, signed in using a bogus name and got his key.

They walked in silence to the room that was farthest from the office window and where Dean had parked his car, had it been any other night, the long trip would have made the fire in him quell to something like an ember but instead Dean felt like a wildfire had been set ablaze in his veins. Each step he took that got him and the tall stranger to room 27 made the intense inferno in him roar bigger, brighter and hotter. 

They reached their room door and Dean slipped the key into the lock and opened the door, letting the man behind him walk in first. As soon as the door closed behind Dean, he was pushed against it, a hard body pressed against his, lips sliding against his own and a tongue pushing itself into his mouth as a hand cupped and rubbed at his half hard cock. 

“Name’s Sam and after tonight, you won’t be able to stop your dick from getting hard when you hear my name.” Sam whispered against Deans lips, his hand grinding harder against Dean’s crotch, making the dick hidden behind the denim fill further into hardness, that was the only preamble for the kiss that followed. It was filthy, wet, and hungry despite it being too slow for Dean. The slick slide of wet lips was a delicious slow burn with the occasional nip of teeth to his plump lower lip.

Sam guided them over to the bed, pulling out a condom and a bottle of travel size lube and dropping them on one of the pillows. Clothes were tugged and pulled off, the mattress sinking and creaking under their weight and the stiff sheets creasing and wrinkling around them. Dean was laid out on his back, Sam hovering over him his crotch flush against Deans, their dicks semi hard as Sam rolled his hips against Deans. The slide of their cocks was slow and rough making him throw his head back and moan with each roll of Sam’s hips. Dean fisted the sheets when he felt a warm hand wrap around his dick, it felt smooth with a just the barest hint of callousness as it loosely gripped his dick and jerked it lazily.

Sam continues his languid pace, gently teasing the head, sliding the pad on his index finger of the slit, working the beads of precum into the shaft to make the slide of his hand a little smoother, until Dean’s cock is hard and flush in his hand. When Dean is a bucking mess under him, Sam lets go of his rigid cock, it stands at attention against Deans abdomen, flushed, slightly curved and the head looking and angry shade of red. With a few nudges and pushes, Sam gets Dean to roll onto his stomach, parts his cheeks and without and hesitation licks at the hidden pucker. Dean moans and curses under him as Sam continues to lick and flick his tongue against the tight ring of muscles. He laved at it until spit was dripping down Deans cheeks and Sams chin, working the muscle open with both his tongue and the tip of his thumb. When Sam pulled away and reached for the bottle of lube, Dean wasn’t as hard as he had been when the man had flipped him over; he heard the click of the cap being opened and the squelch of the lube being squeezed out of the plastic bottle. Dean waited patiently for Sam to continue his work, when he did, the tip of his lubed up fingers were warm and pressed hard against his hole. Dean willed himself to relax and let the digit sink into him, there was only minor discomfort as Sam worked his finger into Dean in minuscule thrusts, but Dean was able to feel when Sam pushed in past the second joint of his finger and press all the way in. Sam pulled his finger out and then repeated the process, his long finger working the tight ring and pulling it out slowly, shifting it while it was inside. 

When he pressed in again, the fit was tighter as he added a second finger with more lube. The slide in was slow again and Dean felt a slight burn as he was worked open. Sam pushed his fingers forward, scissoring the digits between small thrusts, making Dean whine and buck his hips, desperate for Sam to be in deeper and for his now leaking cock to have some friction. 

“Fuck me harder, I ain’t gonna break.” Dean says through gritted teeth.

There is no answer from behind him, just the hard push of fingers that dive all the way in and pull out just as fast. Dean whines in the back of his throat as Sam thrusts into him hard and without mercy, the high pitched cries become moans after a handful of hard pumps, accentuated with the occasional  _ fuck, yes, harder.  _ When Dean starts moving his hips in earnest, chasing down his orgasm, a strong hand pressed into the small of his back and keeps him from moving, pinning him in place as he’s opened further, the fingers in him relentless as they scissor him. 

The pair of fingers are pulled out with an obscene sounding squelch, and after a long beat there is pressure again at his entrance, but not the kind he had been expecting. Dean had been sure that what would be pressing against his hole would be the latex covered tip of the man’s cock, but instead he felt the slicked tips of 3 fingers. He groaned as the digits sunk in, the careful thrusts forgotten. Sam was sinking his fingers into Dean in sharp quick thrusts, spreading his fingers within the confines of the ring of muscle, with each splay of his fingers the ring giving way a little bit. 

The room was a lullaby of Deans moans and the muted squelching of Sam working his fingers into Dean, who wasn’t paying much attention to the movement that Sam was doing, all he was concerned with was the hard and deep thrusts that were aiding Dean in chasing his orgasm. It was in one particularly hard and deep thrust that Dean arched off the bed and saw stars behind his eyes. Heat flooded every inch of him, as a hoarse  _ YES! _ was ripped out of Deans throat. 

There was another thrust at the exact same spot that resulted in the exact same reaction from Dean, followed by a chuckle from the man behind him. 

“Get on your knees.” Came the whispered command beside his ear, the voice was thick with lust and the breath that fanned across his skin made him feel too hot and ready to explode. 

Dean pushed himself off the bed, it was a bit awkward and uncomfortable as Sam hadn’t removed his fingers and the digits shifted with his movements. Dean settled himself on his hands and knees and waited for Sam to start moving again.

There was a second that passed where Sam didn’t move and Dean was able to see his dick, it was harder than he had ever felt, hanging heavy between his legs and a delicious shade of red; a string of precum connecting the slit of his head to the wet spot on the mattress. 

An arm wrapped around him, the hand splaying over his chest and he was pushed up, to that he was kneeling on the bed, the fingers embedded in his ass shifting with the movement and pressing against the soft gland, making him see stars once again. 

“Better hold on.” Sam said as his hand snaked down and wrapped around his dick once again, but instead of pumping the shaft, it circled the bade of Deans dick in a vice-like hold an the fingers in him started to move again, each thrust pressing hard against his prostate. One of Deans hands flew to the hand holding his dick, if to push it off or help him maintain his hold on it, he wasn’t sure; after futile attempts to decide, he settled with gripping Sam’s wrist, his other hand had a death grip on Sam’s neck, and it was nothing short of a miracle that kept both men upright. After one final thrust against his prostate, where he not only pressed against it, but pushed and rubbed against it, Sam pulled out his fingers. After a pause in which Dean couldn’t hear much due to the rushing blood in his ears and the attention that was solely focused on the hand on his dick, there was a new pressure at his entrance, larger, fuller, and hotter. It pressed in without hesitation or mercy, stretching him further with each in that was pushed forward. 

When Sam was fully inside, he paused, breathing heavily against Deans shoulder, but Dean wasn’t having any of that. He shifted his hips and clenched the monster of a dick that was in his ass. 

“Move.” He gritted out, shifting again making the man in him moan, the sound was like a taste of heaven, it snaked in through his ears and went straight to his abused dick. 

The following snap of Sam’s hips is brutal, pulling out until only the tip of his head is in Dean, then pushing in all the way to the hilt. He fucks him in that manner until they are both a moaning and groaning mess of limbs; the sound of skin slapping against skin joins the chorus of their voices. 

Dean felt his cock throb in Sam’s grip, on the cusps of exploding with each thrust of Sam’s cock. 

“…cum…wanna…need to…” Dean said in the midst of hoarse moans.

“How?” Sam gritted into his shoulder, his hips slowing down.

Dean was too strung out from sex to tell him that he wanted to cum facing him, that he wanted Sam to let go of his cock, fuck him and shoot string after string of his spunk on his abs, or shoot down his throat and watch him swallow his jizz. When he is able to open his mouth to talk around a moan Sam pulls out completely and rams back in at the perfect angle and Dean is shooting his spunk past Sam’s grip, making him slump forward as he heaves and feels the bones afterglow of an epic orgasm. 

After a few more pumps, Sam pulled out and flopped beside Dean, both breathing heavy, sated and boneless. 

Deans turned his head to the left, and as he saw the man beside him, he knew that he had been right. There was no way he was going to be able to stop himself from popping out a random woody at the mention of his name.

 

Bonus (fluffy??) wincest ending:

“You ok?” asked Sam, bringing a hand to rest at Deans shoulder. 

“Yeah, fine.” Dean mutters, his voice is hoarse and a little too raw. 

“I think I was too hard this time.”

Dean gave a small chuckle, mirth coloring his words.

“Not hard enough if you ask me.”

If he was being honest, Sam hadn’t fucked him this good in a long time, it was a welcomed change from the soft and tender lovemaking they shared. 

“I think this roleplaying thing is gonna be great for us.” Dean mumbled as his eyes began to slip close. 

Sam chuckled beside him, and grunted in agreement. 

Deans mind was already racing with other possible scenarios, jock who likes to take a load on his face from the hot nerd, mechanic who is bent over a car and gets his ass pounded by a guy who wants an oil change just to name a couple. Despite the growing list that was working itself in his mind, he was sure to revisit this particular set of roles. 

There was just something about picking Sam up as a prostitute that made his dick twitch and make a valiant effort to come back to life. 

Beside him Sam smiled, and muttered a lazy, 

“Rest up, we’ll be starting round 2 once I’m don’t catching my breath.”

Dean groaned and he felt the blood begin to rush to his cock, because if there was something he loved more than getting fucked into the mattress hard and rough, was getting pushed up on hands and knees, his over sensitive cock hanging between his legs and getting rammed raw until he was hard and shooting his spunk again. 

“Ready when you are.” He said his smile spreading wickedly over his lips. “This time, don’t use the condom.”


End file.
